I want to look stylish but keep my head warm this winter. What would you suggest?
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I have always struggled to find a winter hat that is both dressy and warm. Are there any styles you can recommend?

The answer

Dressy and warm are obvious requirements, but another, less obvious one is that the hat suit your face shape and personality.

While I have no way of determining these factors, I reached out to Karyn Gingras of Lilliput Hats in Toronto. Without much hesitation, she suggested the 1920s-style cloche as a versatile, flattering best bet. “They tend to come down over the ears, which makes them perfect for Canadian winters,” she explained.

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But what convinced me was this: “In fashion history, it’s one of the only periods that [can be riffed on] without [making you look] like you’re dressing in costume.”

She recommends buying a hat made of natural fibres such as merino wool, boiled wool or rabbit-fur felt (which is brushed like angora and then felted). Alternatively, you could certainly add brooches or netting to dress up a beanie (as Jil Sander showed last year), but Gingras rightly notes that the cloche has structure and renewed relevance, in light of Downton Abbey and The Great Gatsby.

Most of all, a cloche conveys an ineffable special-occasion spirit that is invaluable when braving winter’s worst.